Boron Trichloride → Methyl (4'-hydroxy-1,1'-biphenyl-4-yl)acetate

HRID 2076583Notes

Reaction equation

HRID 2076583 reaction equation
B(Cl)(Cl)Cl.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 75488472Methyl 2-[4-(4-methoxyphenyl)phenyl]acetate

Product 1

HCID 86088038Methyl (4'-hydroxy-1,1'-biphenyl-4-yl)acetateYield 78%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

After boron trichloride (1.0N methylene chloride solution 2.0 ml, 2.0 mmol) was added to a solution of methyl (4′-methoxy-1,1′-biphenyl-4-yl)acetate (210 mg, 0.82 mmol) obtained in Example (6-1) and tetra-n-butyl ammonium iodide (393 mg, 1.1 mmol) in methylene chloride (5 ml) at −78° C., the temperature of the mixture was raised to room temperature and then the mixture was stirred for 1 hour. After ice was added to the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=1/1) to give methyl (4′-hydroxy-1,1′-biphenyl-4-yl)acetate (155 mg, yield: 78%).

Workup

  1. additionAfter ice was added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c5030f4578644053861657a743519acd
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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